I would think leeward would be preferable. The power boat
operator will have better control stemming the wind
and will be less likely to do damage. Plus, he'll have cleaner water
to maneuver in and will have an easier time breaking off.
Remember there is suction when two moving boats are alongside. If there is suction AND wind pressure holding him on, he may really have to gun it to get off.
I can imagine exceptions, but generally downwind approach will be easier for the power boat
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